A rainbow of acridinium chemiluminescence

Abstract

Multicolor chemiluminescent acridinium derivatives were synthesized by attaching various common fluorophores to the N 10 -acridinium position through a piperazine linker. Triggering of each acridinium derivative using alkaline hydrogen peroxide resulted in a chemiluminescence spectrum dominated by a strong emission (>95%) from the attached fluorophore. The highly quenched emission from the triggered acridinium, acting as a donor, points to a highly efficient intramolecular energy transfer in acridinium-based chemiluminophore-fluorophore tandems. A variable, and in many cases minimal, spectral overlap between the donor emission and the acceptor absorption may indicate that in such tandems the energy transfer follows the Dexter electron exchange mechanism. Moreover, fluorophores affixed through the acridinium 9-position produce a typical acridinium emission profile, demonstrating the need for close distances and favorable intramolecular orientation of the donor and acceptor moieties for the energy transfer to occur. A family of red-shifted chemiluminescent labels, all sharing a uniform triggering method, will find immediate application in multicolor ligand-receptor assays. Along with the multiplexing capabilities, the red-shifted chemiluminescent detection offers a higher tolerance to green-colored biological interferences and will therefore benefit many screening and diagnostic clinical tests.

Novel Near-Infrared Iridium(III) Complex for Chemiluminescence Imaging of Hypochlorous Acid

“…In most reported CL processes, a high-energy molecule (usually a dioxetane) has been proposed as a putative CL intermediate, which goes back to its ground state by releasing some of its energy as photons of light. 28,30,50,51 In our new CL system, there was still a lack of evidence for the direct observation of similar high-energy intermediates since these intermediates are usually very unstable and low-abundant species. The only certainty appeared to be the observed new CL phenomenon, which was probably due to some highenergy intermediates formed during the HClO-induced oxidative deoximation process, and similar CL phenomenon had also been observed in HClO-participated oxidation of several other organic oximes (Figure S18) accompanied by the generation of similar products such as carboxylic acids (Figures S19−S21 and Tables S3−S5).…”

What Other Than Acridinium Esters? Computational Search for New Acridinium-Based Chemiluminogens

“…However, mainly organic chemiluminogens have several applications, especially as chemiluminescent indicators [19] and chemiluminogenic fragments of chemiluminescent labels [20]. One of the groups of compounds that has found numerous applications in medical [21,22], chemical [2,23], biochemical [24], and environmental [25,26] analysis are acridine derivatives, especially acridinium esters [2,4,5,26,27]. This group of chemiluminogens is characterized by high chemiluminescence efficiency (reaching several percent vs. ~1.3% obtained with luminol) [4,27,28] without the necessity of using a catalyst to initiate chemiluminescence and a low level of background [29].…”

“…One of the groups of compounds that has found numerous applications in medical [21,22], chemical [2,23], biochemical [24], and environmental [25,26] analysis are acridine derivatives, especially acridinium esters [2,4,5,26,27]. This group of chemiluminogens is characterized by high chemiluminescence efficiency (reaching several percent vs. ~1.3% obtained with luminol) [4,27,28] without the necessity of using a catalyst to initiate chemiluminescence and a low level of background [29]. Additionally, these compounds are easily synthesized [4,5,8,30].…”

Europium functionalized black phosphorus quantum dots as a CRET platform for synergistically enhanced chemiluminescence

“…1 It has been shown to have powerful applications in the field of life analysis, environmental monitoring, clinical diagnosis and drug delivery on the basis of its excellent characteristics – no need for a light source, simple apparatus, diverse reaction designs and so on. 2 Recently, many studies have been developed to construct new CRET platforms and enhance luminescence signals by introducing energy receptors (fluorescent molecules, inorganic nanoparticles and rare earths) to expand the practical applications. 3 Limited by the efficiency of the effective energy transfer radius (less than 10 nm), many strategies have been used to shorten the distance between the energy donor and the energy receptor, including the micelle, core–shell structure, coating and doping, to improve the energy transfer efficiency and realize enhancement of a chemiluminescence (CL) signal.…”